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OChem Blows

Organic Chemistry Blows Goat

QuestionAnswer
Hydroxide ion removes a proton from alpha-Carbon of the keto tautomer, forming enolate ion. Enolate ion has two resonance contributors. Protonation on oxygen forms enol tautomer, but protonation on alpha-carbon yields keto tautomer. Base-Catalyzed Keto-Enol Interconversion
The acid protonates the carbonyl oxygen of keto tautomer. Water removes a proton from the alpha-carbon, forming the enol tautomer. Acid-Catalyzed Keto-Enol Conversion
A base removes a proton from the alpha-carbon, forming an enolate in. The enolate ion reacts with an electrophile. Base-Catalyzed Alpha-Substitution
The acid protonates the oxygen, the most electron-dense atom in the molecule. Water removes a proton from the alpha-carbon. The enol reacts with an electrophile. Acid-Catalyzed Alpha-Substitution
The carbonyl oxygen is protonated. Water removes a proton from the alpha-carbon, forming an enol. The enol reacts with an electrophilic halogen. The very acidic protonated carbonyl group loses a proton. Acid-Catalyzed Halogenation
The hydroxide ion removes a proton from the alpha-carbon, forming an enolate ion. The enolate ion reacts with the electrophilic halogen. Base-Promoted Halogenation
All of the hydrogens of the methyl group are replaced by halogens. The product is a trihalo-substituted ketone. Hydroxide ion attacks carbonyl carbon of trihalo-substituted ketone. Transfer of a proton forms carboxylate ion and iodoform. Haloform Reaction
PBr3 converts the carboxylic acid into an acyl bromide. The acyl bromide is in equilibrium with its enol. Bromination of the enol forms the alpha-brominated acyl bromide, which is hydrolyzed to the alpha-brominated carboxylic acid Hell-Volhard-Zelinski Reaction
A base removes a proton from the alpha-carbon of the carbon acid. The enolate ion adds to the beta-carbon of an alpha,beta-unsaturated carbonyl compound. The alpha-carbon is protonated. Michael Reaction
A base removes a proton from the alpha-carbon, creating an enolate ion. The enolate ion adds to the carbonyl carbon of a second molecule of the carbonyl compound. The negatively charged oxygen is protonated. Aldol Addition
A base removes a proton from the alpha-carbon, forming an enolate ion. The enolate ion eliminates the OH group, which picks up a proton as it leaves to make it a better leaving group. E1cB reaction
A base removes a proton from alpha-carbon, creating an enolate ion. The enolate ion adds to the carbonyl carbon of a second molecule of the carbonyl compound. The pi bond reforms, eliminating an alkoxide ion. Claisen Condensation
A base removes a proton from the alpha-carbon, creating an enolate ion. The enolate ion adds to a carbonyl carbon. The pi bond reforms, eliminating an alkoxide ion. Dieckmann Condensation
The first stage is a Michael reaction that forms a 1,5-diketone. The second stage is intramolecular aldol addition. Heating the basic solution dehydrates the alcohol. Robinson Annulation
A proton is easily removed from alpha-carbon because it's flanked by 2 ester groups. Resulting alpha-carbanion reacts with alkyl halide, forming alpha-substituted malonic ester. Malonic Ester Synthesis
Heating alpha-substituted malonic ester in acidic aqueous solution hydrolyzes both ester groups to carboxylic acid groups, forming alpha-substituted malonic acid. Further heating decarboxylates 3-oxocarboxylic acid Decarboxylating carboxylic acids
The alcohol displaces the chloride ion from the dimethylchlorosulfonium ion in an Sn2 reaction. The product of the first step loses a proton. An E2 reaction forms the aldehyde (or the ketone). Swern Oxidation
The ketone and the peroxyacid form an unstable tetrahedral intermediate with a weak O-O bond. As the O-O bond breaks heterolytically, one of the alkyl groups migrates to oxygen. Similar to 1,2-shifts Baeyer-Villiger Oxidation
OsO4 forms a cylic intermediate when it reacts with an alkene. Its a syn addition because both oxygens are delivered to same side of double bond. Intermediate is hydrolyzed with aqueous hydrogen peroxide. H2O2 reoxidizes reagent back to OsO4 Cis-Glycol Formation
An elecrophile adds to one of the sp2 carbons and nucleophile adds to the other. E+ at oxygen at one end of ozone w/ nucleophile at other end. Molozonide product is unstable due to two O-O bonds, immediately rearranges to more stable ozonide Ozonide Formation
Created by: 655505437